Herbicidal 2-(phenoxy or phenylthio)-2-(,3,5-triazinyloxy) alkanoic acids

ABSTRACT

2-(Phenoxy or phenylthio)-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoic acid compounds, such as ethyl 2-(2-fluorophenoxy)-2-(4,6-dimethylpyrimidin-2-yloxy)-acetate, were prepared by the reaction of a phenol or thiophenol compound with a 2-chloro-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoate ester compound or by the reaction of a pyrimidinol or 1,3,5-triazinol with a 2-bromo-2-(phenoxy or phenylthio)alkanoate ester. These compounds, and, especially, agriculturally acceptable salts, esters, and amides of these compounds, were found to have herbicidal utility.

This is a division of application Ser. No. 07/692,742, filed Apr. 29,1991.

BACKGROUND OF THE INVENTION

The present invention relates to substituted 2-(phenoxy orphenylthio)-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoic acidcompounds and their salts, esters, and amides, to herbicidalcompositions containing these compounds, and to their use as herbicides.

The efficient production of quality food and fiber is highly dependenton the availability of effective herbicides that are safe to man and theenvironment to control undesirable vegetation. New compounds that areuseful in this regard are continuously sought and when found highlyprized.

Certain 2-(pyrimidinyloxy- and 1,3,5-triazinyloxy)alkanoic acids andtheir esters are known to possess herbicidal activity (see, for example,U.S. Pat. No. 4,968,340). Such compounds, however, generally lack therequisite high herbicidal activity and/or selectivity to crops and/orthe low toxicity to man and the environment required to gain broadacceptance.

SUMMARY OF THE INVENTION

It has now been found that 2-(phenoxy or phenylthio)-2-(pyrimidinyloxy,or 1,3,5-triazinyloxy)alkanoic acid compounds are highly herbicidal, areselective toward valuable crops, and degrade in the environment at anacceptable rate.

The invention includes compounds of Formula I: ##STR1## wherein

Q and Q' each independently represent N or C-Y", with the proviso thatat least one of Q and Q' represents N;

Y, Y', and Y" each independently represent H, R¹, OR¹, SR¹, NR² ₂, F,Cl, or Br;

X¹ and X⁵ each independently represent H, F, Cl, Br, or (C₁ -C₄)alkyloptionally mono- or disubstituted with fluorine;

X² and X⁴ each independently represent H, F, Cl, Br, (C₁ -C₄)alkyloptionally mono- or disubstituted with fluorine, SR¹, OR¹, or O-phenyl,O-pyridinyl, or O-pyrimidinyl each optionally substituted with up to twosubstituents selected from F, Cl, Br, CF₃, CH₃, and CN;

X³ represents H or F;

with the proviso that of X¹, X², X³, X⁴, and X⁵ at least two represent Hand at least three represent H or F;

Z represents O or S;

R represents H, (C₁ -C₃)alkyl, CO₂ H, CN, CF₃, or F;

R¹ represents (C₁ -C₃)alkyl optionally singly to completely substitutedwith fluorine; and

R² represents H or (C₁ -C₃)alkyl;

or an agriculturally acceptable salt, ester, and amide thereof.

The compounds of Formula I and, especially, the agriculturallyacceptable salts, esters, and amides thereof are combined withagriculturally acceptable adjuvants and carriers to prepare herbicicalcompositions.

The compounds of Formula I and their agriculturally acceptable salts,esters, and amides are useful as herbicides for the control ofundesirable vegetation when applied either preemergence or postemergenceand can be used to control undesirable vegetation in valuable crops byapplying them to the undesirable vegetation or the locus thereof. Theherbicidal effect is obtained whether a compound of Formula I, anagriculturally acceptable salt, ester, or amide thereof, or any othercompound that degrades in the plant or in the environment to a compoundof Formula I is applied. That is, undesirable vegetation is controlledby applying any compound that results in a compound of Formula I beingpresent within the tissue of the undesirable vegetation. It is preferredto apply an agriculturally acceptable salt, ester, or amide of acompound of Formula I.

DETAILED DESCRIPTION OF THE INVENTION

The compounds of the invention are the compounds described by Formula Iwherein Q and Q' each independently represent N or C-Y" (with theproviso that at least one of Q and Q' represents N); Y, Y', and Y" eachindependently represent H, R¹, OR¹, SR¹, NR² ₂, F, Cl, or Br; X¹ and X⁵each independently represent H, F, Cl, Br, or (C₁ -C₄)alkyl optionallymono- or disubstituted with fluorine; X² and X⁴ each independentlyrepresent H, F, Cl, Br, (C₁ -C₄)alkyl optionally mono- or disubstitutedwith fluorine, SR¹, OR¹, or O-phenyl, O-pyridinyl, or O-pyrimidinyl eachoptionally substituted with up to two substituents selected from F, Cl,Br, CF₃, CH₃, and CN; X³ represents H or F; with the proviso that of X¹,X², X³, X⁴, and X⁵ at least two represent H and at least three representH or F; Z represents O or S; R represents H, (C₁ -C₃)alkyl, CO₂ H, CN,CF₃, or F; R¹ represents (C₁ -C₃)alkyl optionally singly to completelysubstituted with fluorine; and R² represents H or (C₁ -C₃)alkyl; and theagriculturally acceptable salts, esters, and amides of these compounds.The base compounds can be described as 2-phenoxy-2-((2- or4-)pyrimidinyloxy or 2-(1,3,5-triazinyloxy))alkanoic acids optionallypossessing selected substituents on the phenyl, pyrimidinyl, triazinyl,and alkanoic acid moieties.

Compounds of Formula I wherein each of X¹, X², X³, X⁴, and X⁵ representsH (unsubstituted phenyl compounds); wherein X¹ represents F and X², X³,X⁴, and X⁵ represent H (2-fluorophenyl compounds); wherein X² representsF and X¹, X³, X⁴, and X⁵ represent H (3-fluorophenyl compounds); whereinX¹ and one of X⁴ and X⁵ represent F and X², X³ and the other of X⁴ andX⁵ represent H (2,6-, and 2,5-difluorophenyl compounds) are oftenpreferred. Compounds wherein Z represents O are usually preferred(acetal compounds) as are compounds wherein R represents H (acetic acidcompounds). Compounds wherein Q represents N and Q' represents C-H(pyrimidin-2-yl compounds) are preferred in some circumstances andcompounds wherein both Q and Q' represent N (1,3,5-triazin-2-ylcompounds) are preferred in other circumstances. Compounds of Formula Iwherein Y, Y', and Y" each independently represent H, CH₃, or OCH₃ arealso often preferred. Those wherein Y and Y' both represent CH₃ and Y",if present, represents H and are typically more preferred. It is usuallypreferred to employ the acid compounds of Formula I in the form of anagriculturally acceptable ester. Such esters include (C₁ -C₈)alkyl and(C₃ -C₈)alkoxyalkyl esters. Specifically preferred compounds include themethyl, ethyl, propyl, and butyl esters of2-(2-fluorophenoxy)-2-(4,6-dimethylpyrimidin-2-yloxy)acetic acid,2(3-fluorophenoxy)-2(4,6-dimethylpyrimidin-2-yloxy)acetic acid,2-(2,6-difluorophenoxy)-2-(4,6-dimethylpyrimidin-2-yloxy)acetic acid,2-(2,5-difluorophenoxy-2-(4,6-dimethylpyrimidin-2-yloxy)acetic acid;2-(2-fluorophenoxy)-2-(4-methyl-6-methoxypyrymidin-2-yloxy)acetic acid,and 2-(2-fluorophenoxy)-2-(4,6-dimethyl-1,3,5-triazin-2-yloxy)aceticacid.

The compounds of Formula I exist in two enantiomeric isomer formsbecause the carbon atom adjacent to the carboxylic acid moiety isasymmetrically substituted (except in the case where R represents CO₂H). The present invention relates to each of the enantiomeric isomersand to all mixtures of these isomers. It is anticipated that theenantiomeric isomers will both have utility as herbicides but that oneof the enantiomeric isomers will be generally more efficacious than theother.

Agriculturally acceptable salts, esters, and amides are those salts,esters, and amides of the carboxylic acid group(s) of Formula I whichhave a cation, OR³, NH₂, NHR³, or NR³ ₂ moiety that is not itselfsignificantly herbicidal to any crop being treated nor significantlydeleterious to the applicator, the environment, or the ultimate user ofany crop being treated.

Suitable cations include, for example, those derived from alkali oralkaline earth metals and those derived from ammonia and amines.Preferred cations include sodium, potassium, magnesium, and aminiumcations of the formula

    R.sup.5 R.sup.6 R.sup.7 NH⊕

wherein R⁵, R⁶, and R⁷ each, independently represents hydrogen or (C₁-C₁₂)alkyl, (C₃ -C₁₂)cycloalkyl, or (C₃ -C₁₂)alkenyl, each of which isoptionally substituted by one or more hydroxy, (C₁ -C₈)alkoxy, (C₁-C₈)alkylthio or phenyl groups, provided that R⁵, R⁶, and R⁷ aresterically compatible. Additionally, any two of R⁵, R⁶, and R⁷ togethermay represent an aliphatic difunctional moiety containing 1 to 12 carbonatoms and up to two oxygen or sulfur atoms. Salts of the compounds ofFormula I can be prepared by treatment of compounds of Formula I or anester thereof with a metal hydroxide, such as sodium hydroxide,potassium hydroxide, or magnesium hydroxide, or by treatment of acompound of Formula I with an amine, such as ammonia, triethylamine,dimethylamine, hydroxyethylamine, trisallylamine, 2-butoxyethylamine,morpholine, cyclodedecylamine, or benzylamine.

Suitable esters and amides include those wherein each R³ independentlyrepresents (C₁ -C₈)alkyl or (C₃ -C₈)alkenyl, each optionally substitutedwith up to 3 compatible groups selected from (C₁ -C₄)alkoxy, F, Cl, Br,and phenyl, or phenyl optionally substituted with up to 3 groupsselected from F, Cl, Br, CH₃, or CF₃. (C₁ -C₄)Alkyl esters are generallypreferred and methyl and butyl esters are often specifically preferred.

The invention further contemplates the control of undesirable vegetationby treating the vegetation or its locus with a substance that degradesin the environment or in the undesirable vegetation to a compound ofFormula I. The application of such compounds in place of a compound ofFormula I into the tissue of the undesirable vegetation and, thereby torealize the herbicidal action of the compound of Formula I. Many suchcompounds can be envisioned. Thus, those compounds that are readilyoxidized or hydrolyzed in the environment or in plant tissue to acompound of Formula I, such as, for example, compounds wherein thecarboxylic acid moiety is replaced by hydroxymethyl, aminoethyl, formyl,2-carboxyethyl, 5-chloro-2-pentenyl, cyano, 2-dioxolanyl, can all beemployed. The critical feature is that the substance applied places acompound of Formula I within the plant tissue.

The compounds of Formula I can be prepared by the reaction of a hydroxysubstituted heterocycle of Formula II with an optionally substituted2-halo-2-phenoxyalkanoate or 2-halo-2-(phenylthio)alkanoate ester ofFormula III. ##STR2## R⁴ of Formula III represents (C₁ -C₈)alkyl or (C₃-C₈)alkoxyalkyl. Methyl or ethyl esters are often preferred for generaloperations and when the ultimate preparation of a specific ester of acompound of Formula I is desired, it is preferred to employ the sameester of the compound of Formula III. G represents bromine or chlorine,most generally bromine. The reaction is generally carried out by firstconverting an appropriate substituted pyrimidinol or 1,3,5-triazinol toits alkali metal salt by treatment with a strong base, such as sodiumhydride, potassium carbonate, or a tetraalkylammonium hydroxide in aninert solvent, such as tetrahydrofuran or N,N-dimethylformamide, andthen adding an optionally substituted 2-halo-2-(phenoxy orphenylthio)alkanoate ester and allowing the two to react. An ester of acompound of Formula I is formed which can be recovered by conventionalmeans. This ester can be converted to an acid compound of Formula I orto a salt thereof by hydrolysis, to a different ester bytransesterification, or to an amide by treatment with an amine, allusing conventional methods well known in the art.

Optionally substituted 2-bromo-(2-phenoxy)alkanoate and2-bromo-2-(phenylthio)alkanoate esters of Formula III wherein X¹ and X⁵each independently represent H, F, Cl, Br, or (C₁ -C₄)alkyl optionallymono- or disubstituted with fluorine; X² and X⁴ each independentlyrepresent H, F, Cl, Br, (C₁ -C₄)alkyl optionally mono- or disubstitutedwith fluorine, SR¹, OR¹, or O-phenyl, O-pyridinyl, or )-pyrimidinyl eachoptionally substituted with up to two substituents selected from F, Cl,Br, CF₃, CH₃, and CN; X³ represents H or F; with the proviso that of X¹,X², X³, X⁴, and X⁵ at least two represent H and at least three representH or F; R¹ represents (C₁ -C₃)alkyl optionally singly to completelysubstituted with fluorine; Z represents O or S; R represents H, (C₁-C₃)alkyl, CO₂ H, CN, CF₃, or F; and R⁴ represents (C₁ -C₈)alkyl or(C₃ - C₈)alkoxyalkyl that are useful as starting materials for theabove-described process can be prepared by bromination of thecorresponding optionally substituted 2-phenoxyalkanoate ester of2-(phenylthio)alkanoate ester with N-bromosuccinimide by procedures wellknown in the art.

Alternately, the compounds of Formula I can be prepared by the reactionof an optionally substituted phenol or thiophenol with an optionallysubstituted 2-halo-2-(heterocyclyloxy)alkanoate ester of Formula IVwherein R, R⁴, Q, Q', Y, Y', and G are as defined hereinbefore. ##STR3##The reaction can be carried out by adding the optionally substitutedphenol or thiophenol and a base, such as sodium hydride or potassiumcarbonate, to the optionally substituted2-halo-2-(heterocyclyloxy)alkanoate ester in a solvent, such astetrahydrofuran, acetonitrile, or N,N-dimethylformamide. The productobtained, which is an ester of a compound of Formula I, can be recoveredby conventional means.

The optionally substituted 2-halo-2-(heterocyclyloxy)alkanoate esters ofFormula IV wherein Y, Y', and Y" each independently represent H, R¹,OR¹, SR¹, NR² ₂, F, Cl, or Br; R¹ represents (C₁ -C₃)alkyl optionallysingly to completely substituted with fluorine; R represents H, (C₁-C₃)alkyl, CO₂ H, CN, CF₃, or F; and R⁴ represents (C₁ -C₈)alkyl or (C₃-C₈)alkoxyalkyl that are useful as starting materials required for theabove-described process can be prepared by chlorination or brominationof an appropriate optionally substituted 2-(heterocyclyloxy)alkanoateester. This can be accomplished by consecutively adding lithiumhexamethyldisilylamide and the appropriate (2-heterocyclyloxy)alkanoateester to a dry-ice and acetone cooled solution of trimethylsilylchloride in an ether solvent, such as diethyl ether or tetrahydrofuran,and then adding N-chlorosuccinimide or N-bromosuccinimide with stirringand cooling. The 2-halo-2-(heterocyclyloxy)alkanoate ester prepared canbe recovered by removing the water soluble and volatile components ofthe product mixture by extraction and evaporation or by otherconventional methods. These compounds are typically employed asintermediates without further purification.

The 2-(heterocyclyloxy)alkanoate esters employed in the processdescribed above can be prepared either by the reaction of an appropriate2-hydroxyalkanoate ester with an appropriate chloro or methanesulfonylsubstituted pyrimidine or 1,3,5-triazine or by the reaction of anappropriate pyrimidinol or 1,3,5-triazinol with an ester of anappropriate 2-bromoalkanoic acid. Suitable reaction conditions for suchprocesses are well known in the art.

The compounds of the present invention can be used directly asherbicides, but it is generally preferable to first prepare anherbicidal composition containing one or more of the compounds incombination with an agriculturally acceptable adjuvant or carrier.Suitable adjuvants or carriers should not be phytotoxic to valuablecrops, particularly at the concentrations employed in applying thecompositions for selective weed control in the presence of crops, andshould not react chemically with compounds of Formula I or othercomposition ingredients. Such mixtures can be designed for applicationdirectly to plants or their locus or can be concentrates or formulationswhich are normally diluted with additional carriers and adjuvants beforeapplication. They can be solids, such as, for example, dusts, granules,water dispersible granules, or wettable powders, or liquids, such as,for example, emulsifiable concentrates, solutions, emulsions orsuspensions.

Suitable agricultural adjuvants and carriers that are useful inpreparing the herbicidal mixtures of the invention are well known tothose skilled in the art.

Liquid carriers that can be employed include water, toluene, xylene,petroleum naphtha, crop oil, acetone, methyl ethyl ketone,cyclohexanone, trichloroethylene perchloroethylene, ethyl acetate, amylacetate, butyl acetate, propylene glycol monomethyl ether and diethyleneglycol monomethyl ether, isopropyl alcohol, amyl alcohol, ethyleneglycol, propylene glycol, glycerine, and the like. Water is generallythe carrier of choice for the dilution of concentrates.

Suitable solid carriers include talc, pyrophyllite clay, silica,attapulgus clay, kieselguhr, chalk, diatomaceous earth, lime, calciumcarbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheatflour, soybean flour, pumice, wood flour, walnut shell flour, lignin,and the like.

It is frequently desirable to incorporate one or more surface-activeagents into the compositions of the present invention. Suchsurface-active agents are advantageously employed in both solid andliquid compositions, especially those designed to be diluted withcarrier before application. The surface-active agents can be anionic,actionic, or nonionic in character and can be employed as emulsifyingagents, wetting agents, suspending agents, or for other purposes.Typical surface-active agents include salts of alkyl sulfates, such asdiethanolammonium lauryl sulfate; alkylarylsulfonate salts, such ascalcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide additionproducts, such as nonylphenol-C₁₈ ethoxylate; alcohol-alkylene oxideaddition products, such as tridecyl alcohol-C₁₆ ethoxylate; soaps, suchas sodium stearate, alkylnaphthalenesulfonate salts, such as sodiumdibutylnaphthalenesulfonate; dialkyl esters of sulfoccuinate salts, suchas sodium di(2-ethylhexyl) sulfoccinate; sorbitol esters, such assorbitol oleate; quaternary amines, such as lauryl trimethylammoniumchloride polyethylene glycol esters of fatty acids, such as polyethyleneglycol stearate; block copolymers of ethylene oxide and propylene oxide;and salts of mono and dialkyl phosphate esters.

Other adjuvants commonly utilized in agricultural compositions includeantifoam agents, compatibilizing agents, sequestering agents,neutralizing agents and buffers, corrosion inhibitors, dyes, odorant,penetration aids, spreading agents, sticking agents, dispersing agents,thickening agents, freeze point depressants, antimicrobial agents, andthe like. The addition of crop oil and crop oil concentrates is typical.The compositions can also contain other compatible components, forexample, other herbicides, plant growth regulants, fungicides,insecticides, and the like and can be formulated with solid, particulatefertilizer carriers such as ammonium nitrate, urea, and the like or withliquid fertilizers.

The concentration of the active ingredients in the herbicidalcompositions of this invention is generally from about 0.001 to about 98percent by weight. Concentrations from about 0.01 to about 90 percent byweight are often employed. In compositions designed to be employed asconcentrates, the active ingredient is generally present in aconcentration from about 5 to about 98 weight percent, preferably fromabout 10 to about 90 weight percent. Such compositions are typicallydiluted with an inert carrier, such as water, before application. Thediluted compositions usually applied to plants or their locus generallycontain from about 0.001 to about 5 weight percent active ingredient andpreferably contain from about 0.01 to about 1.0 percent. It is preferredto employ an agriculturally acceptable salt, ester, or amide of acompound of Formula I in herbicidal compositions because such compoundsare generally much more stable than are the acids of Formula I.

The present compositions can be applied by the use of conventionalground or aerial dusters and sprayers, by addition to irrigation water,and by other conventional means known to those skilled in the art.

The compounds of the present invention can be used for generalvegetation control at higher application rates or can be employed atlower rates wherein desirable vegetation is unaffected, but undesirablevegetation is controlled. They are especially valuable for the controlof undesirable vegetation in the presence of crop plants. The selectivecontrol of undesirable vegetation in cereal crops, especially in wheatand barley crops, is preferred with most of the compounds and theselective control of undesirable vegetation in corn is preferred with afew.

General herbicide action is usually observed for compounds of Formula I,including the agriculturally acceptable salts, esters, and amidesthereof, at rates of greater than about 2 Kg/Ha for preemergence and 1Kg/Ha for postemergence applications. The selective control ofsusceptible weeds in crops such as wheat and corn can be accomplished atapplication rates of from about 500 g/Ha to about 1 Kg/Ha preemergenceand of from about 10 g/Ha to about 500 g/Ha postemergence. Anappropriate rate for each crop, compound and circumstance can bedetermined by simple range finding tests using the teachings herein.

The term "herbicide" is used herein to mean an active ingredient whichcontrols or adversely modifies growth of plants. By "vegetationcontrolling" or "herbicidally effective" amount is meant an amount ofactive ingredient which causes an adversely modifying effect andincludes deviations from natural development, killing, regulation,dessication, retardation, and the like. The terms "plants" and "weeds"are meant to include germinant seeds, emerging seedlings, andestablished vegetation. "Undesirable vegetation" is plant life presentin a place where it is not wanted.

Herbicidal activity is exhibited by the compounds of the presentinvention when they are applied directly to the plant or to the locus ofthe plant at any stage of growth or before emergence. The effectobserved depends upon the plant species to be controlled, the stage ofgrowth of the plant, the application parameters of dilution and thespray drop size, the particle size of solid components, theenvironmental conditions at the time of use, the specific compoundemployed, the specific adjuvants and carriers employed, and the like, aswell as the amount of chemical applied. These and other factors can beadjusted as is known in the art to promote selective herbicidal action.It is preferred to employ the compounds of Formula I and theiragriculturally acceptable salts, esters, and amides to controlundesirable vegetation by postemergence application.

EXAMPLES Example 1 Preparation of Methyl 2-Bromo-2-phenoxyacetate

Methyl phenoxyacetate (5.0 g, 30 mmol), N-bromosuccinimide (5.4 g, 30mmol), a few crystals (0.2 to 0.5 g) of benzoyl peroxide, and 50 mL ofcarbon tetrachloride were placed in a 100 ml flask and heated at refluxwith stirring for about 4 hr. The mixture was then allowed to cool, wasfiltered, and was concentrated by evaporation under reduced pressure toobtain 6.6 g (90 percent of theory) of the title compound as a red oil.

H¹ NMR (δ, CDCl₃), 3.91 (s, 3H), 6.57 (s, 1H), 7.07-7.60 (m, 5H).

Example 2 Preparation of Methyl2-Phenoxy-2-(4,6-dimethylpyrimidin-2-yl)oxy)acetate

4,6-Dimethyl-2-pyrimidinol (3.0 g, 24 mmol) and 60 mL of tetrahydrofuranwere placed in a dry 250 mL flask and blanketed with argon. Sodiumhydride (1.0 g of 60 percent, 24 mmol) was added carefully and themixture was allowed to stir at ambient temperature for 0.5 hr. Asolution of methyl 2-bromo-2-phenoxyacetate (7.2 g, 29 mmol) in a smallamount of tetrahydrofuran was added dropwise with stirring and themixture was then allowed to stir overnight under argon at ambienttemperature. The resulting mixture was found by thin layerchromatography to contain only a trace of the starting pyrimidinol. Themixture was concentrated by evaporation under reduced pressure and theresidue was diluted with water and ether. The phases that formed wereseparated and the aqueous phase was extracted twice with ether. Thecombined ethereal phase was extracted with water and then dried overmagnesium sulfate, filtered, and concentrated by evaporation underreduced pressure to obtain the title compound in crude form as a reddishoil. This oil was column chromatographed on silica eluting with a 75:25mixture of hexane and ethyl acetate to obtain 1.2 g (17 percent oftheory) of the title compound as a pink oil of 93 percent purity, asdetermined by gas-liquid chromatography.

¹ H NMR (δ, CDCl₃), 2.4 (s, 6H), 3.86 (s, 3H), 6.78 (s, 1H), 6.82 (s,1H), 7.01-7.52 (m, 5H);

¹³ C NMR (δ, CDCl₃), 23.8, 52.9, 93.3, 115.5, 117.5, 123.4, 129.6,156.4, 162.4, 166.5, 169.6.

Alternately, the tetrabutylammonium salt of 4,6-dimethyl-2-pyrimidinolwas first prepared by placing 4,6-dimethyl-2-hydroxypyrimidine (13.0 g,0.105 mol) in a flask, adding 65 g of 40 percent aqueoustetrabutylammonium hydroxide (0.10 mol), and removing the water byevaporation under reduced pressure at pressures down to about 10 mm Hg(1.33 kPa) at 40°-45° C. The residue amounted to 42.7 g and appeared tobe a dihydrate of the desired salt. A 10.9 g portion of this (25 mmol)was placed in a 500 mL flask containing 25 mL of tetrahydrofuran. Acloudy solution formed. To this was added with stirring at ambienttemperature 14 mL of a solution of methyl 2-bromo-2-phenoxyacetate intetrahydrofuran (containing about 25 mmol). The resulting mixture wasallowed to stir for 2 days. Analysis by gas-liquid chromatographyindicated only one significant compound was present. A 250 mL portion ofdiethyl ether was added and the resulting mixture was extracted 5 timeswith 100 mL portions of water and then with brine. The ethereal solutionwas dried over magnesium sulfate, filtered, and concentrated byevaporation under reduced pressure to obtain the title compound in crudeform as a dark brown oil. This was filtration chromatographed on silicagel eluting first with a 10:90 mixture of diethyl ether and hexane andthen with a 15:85 mixture of ethyl acetate and hexane. The productcontaining eluate was concentrated by evaporation under reduced pressureto obtain 2.50 g (35 percent of theory) of the title compound as a paleyellow oil. This oil solidified on standing to a light orange solidmelting at 50°-53° C.

Example 3 Preparation of Ethyl 2-(4,6-Dimethyl-2-pyrimidinyloxy)acetate

A solution containing 4,6-dimethyl-2-methylsulfonylpyrimidine (10.0 g,53.8 mmol), ethyl glycolate (5.60 g, 53.8 mmol), and 30 mL ofN,N-dimethylformamide was prepared and to this was added with stirringpotassium carbonate (8.0 g, 60 mmol). The mixture was allowed to stir atambient temperature overnight. It was then poured into water and theresulting mixture was extracted 3 times with ethyl acetate. The combinedorganic extracts were extracted with water. The aqueous extract wassaturated with sodium chloride and extracted twice more with ethylacetate. All of the ethyl acetate layers were combined, dried overmagnesium sulfate, filtered, and concentrated by evaporation underreduced pressure to obtain 8.20 g (72.6 percent of theory) of the titlecompound as a yellow oil. This oil was filtration chromatographed onsilica gel, eluting with a 30:70 mixture of ethyl acetate and hexane.The product containing eluate was concentrated by evaporation underreduced pressure to obtain 7.9 g (70 percent of theory) of the titlecompound as a colorless oil which solidified on standing to a whitesolid melting at 57°-59° C.

Example 4 Preparation of Ethyl2-Chloro-2-(4,6-dimethyl-2-pyrimidinyloxy)acetate

A solution of trimethylsilyl chloride (0.70 mL, 0.60 g, 5.5 mmol) andethyl 2-(4,6-dimethyl-2-pyrimidinyloxy)acetate (1.0 g, 4.8 mmol) in 4 mLof tetrahydrofuran was prepared and cooled to -78° C. with adry-ice/acetone bath and to this was added with stirring a 1M solutionof lithium hexamethyldisilylamide in tetrahydrofuran (5.5 mL, 5.5 mmol).The solution, which became yellowish orange, was stirred for 15 minutesand then N-chlorosuccinimide (0.70 g, 5.2 mmol) was added with stirringand cooling. After a few minutes the mixture was allowed to warm andabout 50 mL of hexane was added. The resulting solution was extractedwith water three times, dried over magnesium sulfate, and concentratedby evaporation under reduced pressure to obtain a pasty oil. This wasredissolved in hexane and the resulting solution filtered andconcentrated under reduced pressure to obtain 0.65 g of the titlecompound as a yellow oil that was about 63 percent pure as determined bygas-liquid chromatography.

Example 5 Preparation of Methyl2-(3-Phenoxyphenoxy)-2-(4,6-dimethyl-2-pyrimidinyloxy)acetate

3-Phenoxyphenol (1.0 g, 5.4 mmol) was placed in a flask with potassiumcarbonate (0.90 g, 6.5 mmol) and 20 mL of acetonitrile and to this wasadded dropwise with stirring at ambient temperature, a solution of ethyl2-chloro-2-(4,6-dimethyl-2-pyrimidinyloxy)acetate (1.40 g, 5.7 mmol) in5 mL of acetonitrile. The mixture was allowed to stir overnight and wasthen added to water and the resulting mixture was extracted 3 times withether. The ethereal solution was extracted 2 times with 1N aqueoussodium hydroxide, dried over magnesium sulfate, filtered, andconcentrated by evaporation under reduced pressure to obtain about 1 gof the title compound as a crude yellow oil. This oil, which solidifiedon standing, was chromatographed on silica eluting with an 85:15 mixtureof hexane and ethyl acetate to obtain 0.60 g (28 percent of theory) ofthe title compound as a white solid melting at 111°-112° C.

Example 6 Preparation of Sodium2-(2-Fluorophenoxy-2-(4,6-dimethylpyrimidin-2-yloxy)acetate

Ethyl 2-(2-fluorophenoxy-2-(4,6-dimethyl-2-pyrimidinyloxy)acetate (0.3g, 0.94 mmol) was placed in a 25 mL flask with 10 mL of tetrahydrofuranand 0.84 mL (0.84 mmol) of 1N sodium hydroxide solution was added withstirring. The mixture was stirred at ambient temperature overnight afterwhich only a trace of starting ester remained as determined by thinlayer chromatography using silica and a 70:30 mixture of hexane andethyl acetate. The mixture was concentrated by evaporation under reducedpressure and the residue diluted with water and ether. The aqueous andorganic layers were separated and the aqueous layer was extracted twicewith ether. It was then concentrated by evaporation under reducedpressure to obtain 0.25 g (85 percent of theory) of the title compoundas a white solid.

The compounds listed in Table I were prepared by the methods describedin Examples 2, 5, and 6 as indicated in Table I. The proton nuclearmagnetic resonance absorptions of a number of the ester and amideproducts are given in Table Ia.

                                      TABLE I                                     __________________________________________________________________________    EXAMPLES OF COMPOUNDS OF THE INVENTION                                         ##STR4##                                                                        X.sup.1, X.sup.2                                   Elemental                  X.sup.3, X.sup.4                                                                    Y, Y'                      Made              Analysis,                  & X.sup.5                                                                           & Y"                       by  Yield,  Melting                                                                             Percent                 Cpd                                                                              (other                                                                              (other                     Ex. Per-    Point,                                                                              Calc./Found             No.                                                                              than H)                                                                             than H)                                                                              Z M    Q   Q'  R    No. cent                                                                              Form                                                                              °C.                                                                          C  H  N                 __________________________________________________________________________     1 --    Y = CH.sub.3                                                                         O OCH.sub.3                                                                          N   CH  H    2   35  orange                                                                            50-53 62.5                                                                             5.59                                                                             9.72                       Y' = CH.sub.3                      solid     62.3                                                                             5.74                                                                             9.57               2 --    Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             168-170                                Y' = CH.sub.3                      solid                              3 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   28  yellow    60.0                                                                             5.31                                                                             8.75                       Y' = CH.sub.3                      oil       59.7                                                                             5.36                                                                             8.59               4 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             149-151                                Y' = CH.sub.3                      solid                                                                             (d)                            5 X.sup.2 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   15  yellow    56.8                                                                             4.73                                                                             8.28                 X.sup.4 = F                                                                         Y' = CH.sub.3                      oil       56.8                                                                             4.62                                                                             8.00               6 X.sup.2 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             144-146                          X.sup.4 = F                                                                         Y' = CH.sub.3                      solid                              7 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   13  yellow    56.8                                                                             4.73                                                                             8.28                 X.sup.3 = F                                                                         Y' = CH.sub.3                      oil       56.6                                                                             4.82                                                                             8.15               8 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             129-132                          X.sup.3 = F                                                                         Y' = CH.sub.3                      solid                              9 X.sup.2 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   17  yellow    56.8                                                                             4.73                                                                             8.28                 X.sup.3 =  F                                                                        Y'= CH.sub.3                       oil       57.0                                                                             4.72                                                                             7.99              10 X.sup.2 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             129-132                          X.sup.3 = F                                                                         Y' = CH.sub.3                      solid                             11 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   26  yellow    56.8                                                                             4.73                                                                             8.28                 X.sup.4 = F                                                                         Y' = CH.sub.3                      oil       56.7                                                                             4.62                                                                             8.09              12 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             115-118                          X.sup.4 = F                                                                         Y' = CH.sub.3                      solid                             13 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   20  yellow    56.8                                                                             4.73                                                                             8.28                 X.sup.2 = F                                                                         Y' = CH.sub. 3                     oil       56.5                                                                             4.67                                                                             7.95              14 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             150-153                          X.sup.2 = F                                                                         Y' = CH.sub.3                      solid                             15 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   18  yellow    56.8                                                                             4.73                                                                             8.28                 X.sup.5 = F                                                                         Y' = CH.sub.3                      oil       55.7                                                                             4.59                                                                             8.12              16 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             134-136                          X.sup.5 = F                                                                         Y' = CH.sub.3                      solid                                                                             (d)                           17 X.sup.3 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   28  yellow    60.0                                                                             5.31                                                                             8.75                       Y' = CH.sub.3                      oil       60.0                                                                             5.18                                                                             8.53              18 X.sup.3 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       lt. 120-124                                Y' = CH.sub.3                      brown                                                                             (d)                                                                       solid                             19 X.sup.2 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   15  orange    60.0                                                                             5.31                                                                             8.75                       Y' = CH.sub.3                      oil       59.7                                                                             5.28                                                                             8.66              20 X.sup.2 = F                                                                         Y = CH.sub.3                                                                         O ONa  N   CH  H    6       yellow                                                                            130-133                                Y' = CH.sub.3                      solid                             21 X.sup.1 = Cl                                                                        Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   14  yellow    57.1                                                                             5.05                                                                             8.32                       Y' = CH.sub.3                      oil       56.8                                                                             5.14                                                                             8.23              22 X.sup.1 = Cl                                                                        Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             176-180                                Y' = CH.sub.3                      solid                                                                             (d)                           23 X.sup.1 = Br                                                                        Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2    9  yellow    50.4                                                                             4.46                                                                             7.35                       Y' = CH.sub.3                      oil       50.0                                                                             4.35                                                                             7.32              24 X.sup.1 = Br                                                                        Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             181-184                                Y' = CH.sub.3                      solid                                                                             (d)                           25 X.sup.1 = Cl                                                                        Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   67  color-    52.1                                                                             4.61                                                                             7.60                       Y' = CH.sub.3                      less oil  51.8                                                                             4.54                                                                             7.59              26 X.sup.1 = Cl                                                                        Y = CH.sub.3                                                                         O OH   N   CH  H    6       white                                                                             141(d)                                 Y' = CH.sub.3                      solid                             27 X.sup.1  = F                                                                        Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   CH  N   H    2   19  yellow    60.0                                                                             5.35                                                                             8.75                       Y' = CH.sub.3                      oil       60.0                                                                             5.34                                                                             8.66              28 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O ONa  CH  N   H    6       white                                                                             204-207                                Y' = CH.sub.3                      solid                                                                             (d)                           29 --    Y = OCH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                   N   CH  H    2   40  white                                                                             55-60 56.2                                                                             5.04                                                                             8.75                       Y' = OCH.sub.3                     solid     56.5                                                                             5.44                                                                             8.48              30 --    Y = OCH.sub.3                                                                        O ONa  N   CH  H    6       white                                                                             157-160                                Y' = OCH.sub.3                     solid                             31 X.sup.2 = Cl                                                                        Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2    9  yellow    57.1                                                                             5.05                                                                             8.32                       Y' = CH.sub. 3                     oil       56.8                                                                             5.02                                                                             8.17              32 X.sup.2 = Cl                                                                        Y = CH.sub.3                                                                         O ONa  N   CH  H    6       white                                                                             143-145                                Y' = CH.sub.3                      solid                                                                             (d)                           33 X.sup.2 = F                                                                         Y = CH.sub.3                                                                         S OC.sub.2 H.sub.5                                                                   N   CH  H    2   26  orange    57.1                                                                             5.10                                                                             8.33                       Y' = CH.sub.3                      oil       57.4                                                                             5.32                                                                             8.34              34 X.sup.2 = F                                                                         Y = CH.sub.3                                                                         S ONa  N   CH  H    6       yellow                                                                            101-105                                Y' = CH.sub.3                      crystals                          35 X.sup.2 = Br                                                                        Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2   17  yellow    50.4                                                                             4.50                                                                             7.35                       Y' = CH.sub.3                      oil       50.3                                                                             4.33                                                                             7.06              36 X.sup.2 = Br                                                                        Y = CH.sub.3                                                                         O ONa  N   CH  H    6       amber                                      Y' = CH.sub.3                      glass                             37 X.sup.2 = F                                                                         Y = OCH.sub.3                                                                        S OC.sub.2 H.sub.5                                                                   N   CH  H    2    7  clear     52.2                                                                             4.65                                                                             7.61                       Y' = OCH.sub.3                     oil       52.0                                                                             4.28                                                                             7.70              38 X.sup.2 = F                                                                         Y = OCH.sub.3                                                                        S ONa  N   CH  H    6       white                                                                             146-149                                Y' = OCH.sub.3                     powder                            39 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    2    5  orange    58.8                                                                             4.94                                                                             9.15                                                          oil       59.0                                                                             4.87                                                                             8.57              40 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O NHCH.sub.3                                                                         N   CH  H            white                                                                             128-129                                Y' = CH.sub.3                      solid                             41 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OCH.sub.3                                                                          N   CH  H        12  color-    58.8                                                                             4.90                                                                             9.15                       Y' = CH.sub.3                      less oil  59.0                                                                             5.00                                                                             9.07              42 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.8 C.sub.17                                                                  N   CH  H    2    3  color-    63.4                                                                             7.18                                                                             6.93                       Y' = CH.sub.3                                                                          (n)                       less oil  64.7                                                                             7.49                                                                             6.30              43 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O NH.sub.2                                                                           N   CH  H    2   70  white                                                                             139   57.7                                                                             4.81                                                                             14.4                       Y' = CH.sub.3                      solid     57.6                                                                             4.95                                                                             14.2              44 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O N(CH.sub.3).sub.2                                                                  N   CH  H        23  white                                                                             110-111                                                                             60.2                                                                             5.64                                                                             13.2                       Y' = CH.sub.3                      solid     60.0                                                                             5.79                                                                             13.2              45 X.sup.1 = F                                                                         Y = OCH.sub. 3                                                                       O OC.sub.2 H.sub.5                                                                   N   CH  H    2   21  white                                                                             64-66 51.9                                                                             4.36                                                                             7.57                 X.sup.5 = F                                                                         Y' = OCH.sub.3                     solid     51.4                                                                             4.51                                                                             7.39              46 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   CH  N   H    2   39  clear     56.8                                                                             4.77                                                                             8.28                 X.sup.5 = F                                                                         Y' = CH.sub.3                      oil       56.5                                                                             5.03                                                                             8.07              47 X.sup.1 = F                                                                         Y = OCH.sub.3                                                                        O ONa  N   CH  H    6       white                                X.sup.5 = F                                                                         Y' = OCH.sub.3                     solid                             48 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O ONa  CH  N   H    6       white                                                                             220-224                          X.sup.5 = F                                                                         Y' = CH.sub.3                      solid                             49 X.sup.2 = F                                                                         Y = OCH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                   N   CH  H    2   20  white                                                                             63-64 54.5                                                                             4.86                                                                             7.95                       Y' = OCH.sub.3                     solid     54.4                                                                             4.89                                                                             7.94              50 X.sup.2 = F                                                                         Y = OCH.sub.3                                                                        O ONa  N   CH  H    6       white                                                                             195-197                                Y' = OCH.sub.3                     solid                             51 X.sup.1 = F                                                                         Y = OCH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                   N   CH  H    2   28  white                                                                             74-76 54.5                                                                             4.86                                                                             7.95                       Y' = OCH.sub.3                     solid     54.5                                                                             4.92                                                                             7.58              52 X.sup.1 = F                                                                         Y" = Cl                                                                              O OC.sub.2 H.sub.5                                                                   N   CY" H    2   23  color-    51.5                                                                             3.70                                                                             8.57                                                          less oil  51.5                                                                             3.82                                                                             8.59              53 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         S ONa  N   CH  H    6       beige                                                                             45-55                                  Y' = CH.sub.3                      powder                            54 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         S OC.sub.2 H.sub.5                                                                   N   CH  H    2   18  brown     57.1                                                                             5.10                                                                             8.33                       Y' = CH.sub.3                      oil       57.0                                                                             5.07                                                                             7.95              55 --    Y = CH.sub.3                                                                         S OC.sub.2 H.sub.5                                                                   N   CH  H    2    8  yellow    60.4                                                                             5.66                                                                             8.81                       Y' = CH.sub.3                      oil       59.9                                                                             5.68                                                                             8.65              56 --    Y = CH.sub.3                                                                         S ONa  N   CH  H    6       off-                                                                              138-141                                Y' = CH.sub.3                      white                                                                             (d)                                                                       solid                             57 X.sup.1 = F                                                                         Y = OCH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                   N   N   H    2   65  pale      51.0                                                                             4.56                                                                             11.9                       Y' = OCH.sub.3                     green     51.3                                                                             4.87                                                                             11.7                                                          oil                               58 X.sup.1 = F                                                                         Y = OCH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                   N   CH  H    2   29  pale oil  57.1                                                                             5.09                                                                             8.33                       Y' = OCH.sub.3                               57.3                                                                             5.12                                                                             8.11              59 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O NHOH N   CH  H        63  brown                                                                             100-104                                                                             54.7                                                                             4.56                                                                             13.7                       Y' = CH.sub.3                      solid                                                                             (d)   54.8                                                                             4.97                                                                             12.4              60 X.sup.2 =                                                                           Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    5   27  white                                                                             111-112                                                                             67.0                                                                             5.58                                                                             7.11                 OC.sub.6 H.sub.5                                                                    Y' = CH.sub.3                      solid     67.2                                                                             5.73                                                                             7.08              61 X.sup.2 =                                                                           Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    5   51  yellow    61.4                                                                             6.07                                                                             8.43                 OCH.sub.3                                                                           Y' = CH.sub.3                      oil       61.4                                                                             6.29                                                                             8.40              62 X.sup.1  = CH.sub.3                                                                 Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    5   40  yellow    64.6                                                                             6.33                                                                             8.86                       Y' = CH.sub.3                      oil       64.2                                                                             6.43                                                                             8.74              63 X.sup.2 = CH.sub.3                                                                  Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    5   40  yellow    64.6                                                                             6.33                                                                             8.86                       Y' = CH.sub.3                      oil       64.3                                                                             6.66                                                                             8.90              64 X.sup.1 = F                                                                         Y.sup.1 = OC.sub.2 H.sub.5                                                           O OC.sub.2 H.sub.5                                                                   N   CH  H    2       clear                                      Y.sup.2  = CH.sub.3                oil                               65 X.sup.2 =                                                                           Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H    5   17  yellow    58.6                                                                             5.75                                                                             8.05                 SCH.sub.3                                                                           Y' = CH.sub.3                      oil       58.6                                                                             5.95                                                                             8.04              66 X.sup.1 = Br                                                                        Y = CH.sub. 3                                                                        O OC.sub.2 H.sub.5                                                                   N   CH  H    5   46  white                                                                             103.5-104.5                                                                         41.8                                                                             3.51                                                                             6.09                 X.sup.5 = Br                                                                        Y' = CH.sub.3                      solid     42.0                                                                             3.66                                                                             6.13              67 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   N   H    2   29  pale oil  56.1                                                                             5.02                                                                             13.1                       Y' = CH.sub.3                                56.1                                                                             5.21                                                                             12.9              68 X.sup.2 = O(5-                                                                      Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H                                                 CF.sub.3 -2-                                                                        Y' = CH.sub.3                                                           C.sub.5 H.sub.3 N                                                          69 X.sup.1 = Cl                                                                        Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H                                                 X.sup.5 = Cl                                                                        Y' = CH.sub.3                                                        70 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H                                                 X.sup.5 = Cl                                                                        Y' = CH.sub.3                                                        71 X.sup.1  = F                                                                        Y = Cl O OC.sub.2 H.sub.5                                                                   N   CH  H                                                       Y' = CH.sub.3                                                        72 X.sup.1 = F                                                                         Y = Cl O OC.sub.2 H.sub.5                                                                   N   CH  H                                                       Y' = OCH.sub.3                                                       73 X.sup.1 = F                                                                         Y = OCH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                   N   CH  H                                              74 X.sup.1 = F                                                                         Y = OCHF.sub.2                                                                       O OC.sub.2 H.sub.5                                                                   N   CH  H                                                       Y' = OCHF.sub.2                                                      75 X.sup.1 = F                                                                         Y = OCHF.sub.2                                                                       O OC.sub.2 H.sub.5                                                                   N   CH  H                                                       Y' = CH.sub.3                                                        76 X.sup.1 = F                                                                         Y = CH.sub.2 F                                                                       O OC.sub.2 H.sub.5                                                                   N   CH  H                                                       Y' = CH.sub.3                                                        77 X.sup.1 = F                                                                         Y = CF.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CH  H                                                       Y' = CH.sub.3                                                        78 X.sup.1 = F                                                                         Y" =  CH.sub.3                                                                       O OC.sub.2 H.sub.5                                                                   N   CY" H                                              79 X.sup.1 = F                                                                         Y" = Cl                                                                              O OC.sub.2 H.sub.5                                                                   N   CY" H                                              80 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CY" H                                                       Y" = Cl                                                              81 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   CY" H                                                       Y" = CH.sub.3                                                        82 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   N   H                                                       Y' = OCH.sub.3                                                       83 X.sup.1 = F                                                                         Y = OCH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                   N   N   H                                                       Y' = Cl                                                              84 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   N   H                                                       Y' = Cl                                                              85 X.sup.1 = F                                                                         Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   N   H                                              86 X.sup.1  = F                                                                        Y = OCH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                   N   N   H                                              87 X.sup.2 =                                                                           Y = C.sub.2 H.sub.5                                                                  O OC.sub.2 H.sub.4                                                                   CH  N   CH.sub.3                                          OC.sub.6 H.sub.4                                                                    Y' = OC.sub.2 H.sub.5                                                                  OC.sub.4 H.sub.9                                               Cl(2)                                                                      88 X.sup.2 =                                                                           Y = CH.sub.3                                                                         O OC.sub.2 H.sub.5                                                                   N   N   CN                                                OC.sub.6 H.sub.4                                                                    Y' = NHCH.sub.3                                                         CF.sub.3 (3)                                                               89 X.sup.2 =                                                                           Y = OC.sub.3 H.sub.7                                                                 O N(CH.sub.3)                                                                        CH  N   CF.sub.3                                          OC.sub.6 H.sub.3 -                                                                  Y' = C.sub.3 H.sub.7                                                                   OCH.sub.3                                                      diF(2,4)                                                                   90 X.sup.1 = F                                                                         Y" = CH.sub.3                                                                        O OCH.sub.3                                                                          CY" N   CO.sub.2 CH.sub.3                                 X.sup.2 =                                                                     OC.sub.6 H.sub.5                                                           91 X.sup.1 = F                                                                         --     S OC.sub.3 H.sub.7                                                                   N   CH  C.sub.2 H.sub.5                                   X.sup.4 =      OCH.sub.3                                                      OC.sub.3 H.sub.7                                                           __________________________________________________________________________

                  TABLE Ia                                                        ______________________________________                                        .sup.1 H NUCLEAR MAGNETIC RESONANCE                                           ABSORPTION DATA                                                               Compound                                                                      No.         δ, PPM From Tetramethylsilane (CDCl.sub.3)                  ______________________________________                                         1          2.35(s, 6H), 3.81(s, 3H), 6.71(s, 1H),                                        6.75(s, 1H), 7.0-7.3(m, 5H)                                        3          1.2-1.35(t, 3H), 2.30(s, 6H), 4.2-4.35                                        (q, 2H), 6.67(s, 1H), 6.72(s, 1H),                                            6.85-7.30(m, 4H)                                                   5          1.2-1.35(t, 3H), 2.35(s, 6H), 4.2-4.35                                        (q, 2H), 6.4-6.8(m, 5H)                                            7          1.2-1.35(t, 3H), 2.30(s, 6H), 4.2-4.35                                        (q, 2H), 6.65(s, 1H), 6.70(s, 1H),                                            6.71-7.25(m, 3H)                                                   9          1.2-1.35(t, 3H), 2.35(s, 6H), 4.2-4.35                                        (q, 2H), 6.63(s, 1H), 6.74(s, 1H),                                            6.80-7.15(m, 3H)                                                  11          1.2-1.35(t, 3H), 2.35(s, 6H), 4.2-4.35                                        (q, 2H), 6.6-7.1(m, 5H)                                           13          1.2-1.35(t, 3H), 2.35(s, 6H), 4.2-4.35                                        (q, 2H), 6.72(s, 1H), 6.76(s, 1H),                                            6.8-7.1(m, 3H)                                                    15          1.2-1.35(t, 3H), 2.32(s, 6H), 4.20-4.40                                       (q, 2H), 6.65(s, 1H), 6.68(s, 1H),                                            6.75-7.10(m, 3H)                                                  17          1.2-1.35(t, 3H), 2.35(s, 6H), 4.2-4.35                                        (q, 2H), 6.62(s, 1H), 6.70(s, 1H),                                            6.85-7.15(m, 4H)                                                  19          1.2-1.35(t, 3H), 2.35(s, 6H), 4.2-4.35                                        (q, 2H), 6.70(s, 1H), 7.73(s, 1H),                                            6.75-7.28(m, 4H)                                                  21          1.2-1.35(t, 3H), 2.32(s, 6H), 4.21-4.38                                       (q, 2H), 6.68(s, 1H), 6.74(s, 1H),                                            6.9-7.4(m, 4H)                                                    23          1.2-1.35(t, 3H), 2.30(s, 6H), 4.20-4.40                                       (q, 2H), 6.69(s, 1H), 6.72(s, 1H),                                            6.85-7.55(m, 4H)                                                  25          1.2-1.35(t, 3H), 3.75(s, 6H), 4.25-4.40                                       (q, 2H), 5.72(s, 1H), 6.65(s, 1H),                                            6.93-7.40(m, 4H)                                                  27          1.29(t, 3H, J=7.0), 2.39(s, 3H), 2.40                                         (s, 3H), 4.31(q, 2H, J=7.0), 6.52(s, 1H),                                     6.84(s, 1H), 6.9-7.3(m, 4H)                                       28          2.30(s, 3H), 2.32(s, 3H), 6.52(s, 1H),                                        6.60(s, 1H), 6.9-7.3(m, 4H) (DMSO)                                29          1.31(t, 3H, J=7.1), 4.33(q, 2H, J=7.1),                                       6.76(s, 1H), 6.8-7.3(m, 6H), 7.57(t, 1H,                                      J=8.2)                                                            30          6.40(s, 1H), 6.8-7.3(m, 6H), 7.75(t, 1H,                                      J=8.1) (DMSO)                                                     31          1.2-1.32(t, 3H), 2.32(s, 6H), 4.20-4.35                                       (q, 2H), 6.70(s, 1H), 6.73(s, 1H),                                            6.95-7.27(m, 4H)                                                  33          1.2-1.32(t, 3H), 2.32(s, 6H), 4.20-4.35                                       (q, 2H), 6.67(s, 1H), 6.74(s, 1H),                                            7.0-7.3(m, 4H)                                                    35          1.25-1.35(t, 3H), 2.38(s, 6H), 4.25-4.37                                      (q, 2H), 6.71(s, 1H), 6.75(s, 1H),                                            7.05.7.37(m, 4H)                                                  39          1.20-1.35(t, 3H), 2.4(s, 3H), 4.2-4.4                                         (q, 2H), 6.72(s, 1H), 6.85(d, 1H), 7.0-7.3                                    (m, 4H), 8.32(d, 1H)                                              45          1.31(t, 3H, J=7.2), 3.72(s, 6H), 4.33                                         (q, 2H, J=7.2), 5,71(s, 1H), 6.66(s, 1H),                                     6.8-7.1(m, 3H)                                                    46          1.28(t, 3H, J=7.0), 2.24(s, 3H), 2.33                                         (s, 3H), 4.30(q, 2H, J=7.0), 6.47(s, 1H),                                     6.80(s, 1H), 6.7-7.0(m, 3H)                                       49          1.25-1.35(t, 3H), 3.82(s, 6H), 4.25-4.38                                      (q, 2H), 5.57(s, 1H), 6.61(s, 1H),                                            6.72-6.92(m, 3H), 7.19-7.30(m, 1H)                                51          1.25-1.35(t, 3H), 3.78(s, 6H), 4.25-4.40                                      (q, 2H), 5.74(s, 1H), 6.67(s, 1H),                                            7.0-7.3(m, 4H)                                                    52          1.25-1.35(t, 3H), 4.25-4.44(q, 2H), 6.63                                      (s, 1H), 7.0-7.3(m, 4H), 8.44(s, 2H)                              54          1.15-1.9(t, 3H), 2.35(s, 6H), 4.06-4.14                                       (q, 2H), 6.50(s, 1H), 6.69(s, 1H), 7.0-7.4                                    (m, 3H), 7.6-7.8(m, 1H)                                           55          1.05-1.12(t, 3H), 2.35(s, 6H), 4.00-4.15                                      (q, 2H), 6.50(s, 1H), 6.70(s, 1H), 7.2-7.7                                    (m, 5H)                                                           57          1.25-1.35(t, 3H), 3.95(s, 6H), 4.25-4.40                                      (q, 2H), 6.73(s, 1H), 7.0-7.3(m, 4H)                              58          1.25-1.35(t, 3H), 2.28(s, 3H), 3.80                                           (s, 3H), 4.25-4.4(q, 2H), 6.25(s, 1H), 6.73                                   (s, 1H), 7.0-7.3(m, 4H)                                           59          2.23(s, 6H), 6.92(s, 1H), 7.0-7.3(m, 4H),                                     9.0-9.5(br s) (in DMSO)                                           60          1.20-1.35(t, 3H), 2.35(s, 6H), 4.25-4.35                                      (q, 2H), 6.6-7.4(m, 11H)                                          61          1.25-1.32(t, 3H), 2.38(s, 6H), 3.75                                           (s, 3H), 4.24-4.37(q, 2H), 6.57-6.77                                          (m, 5H), 7.11-7.20(t, 1H)                                         62          1.2-1.35(t, 3H), 2.25(s, 3H), 2.35(s, 6H),                                    4.2-4.35(q, 2H), 6.65(s, 1H), 6.70(s, 1H),                                    6.85-7.2(m, 4H)                                                   63          1.2-1.35(t, 3H), 2.30(s, 3H), 2.35(s, 6H),                                    4.2-4.35(q, 2H), 6.67(s, 1H), 6.70(s, 1H),                                    6.8-7.2(m, 4H)                                                    65          1.2-1.35(t, 3H), 2.35(s, 6H), 2.40(s, 3H),                                    4.2-4.35(q, 2H), 6.70(s, 2H), 6.8-7.2                                         (m, 4H)                                                           66          1.32-1.40(t, 3H), 2.20(s, 6H), 4.32-4.45                                      (q, 2H), 6.65(s, 1H), 6.79-6.89(t, 1H),                                       6.98(s, 1H), 7.40-7.45(d, 2H)                                     67          1.2-1.35(t, 3H), 2.50(s, 6H), 4.25-4.40                                       (q, 2H), 6.76(s, 1H), 7.0-7.3(m, 4H)                              ______________________________________                                    

Example 7 Postemergence Herbicidal Activity

Seeds of the desired test plant species were planted in sandy soilhaving a pH range of about 5-7.5 and an organic matter content of lessthan 0.5 percent in plastic pots with a surface area of 64 square cm.The plants were grown for 7-20 days in a greenhouse with anapproximately 14 hr photoperiod maintained at about 25°-33° C. duringthe day and 15°-20° C. during the night. Nutrients were added on aregular basis and supplemental lighting was provided with an overhead1000 Watt multi-vapor lamp when necessary. The plants were employed fortesting after they reached the first or second true leaf-stage.

A weighed amount of each test compound in a 10 mL glass vial wasdissolved in 4 mL of a 97:3 mixture of acetone and dimethyl sulfoxide toobtain concentrated stock solutions. If the test compound did notdissolve readily, the mixture was warmed and sonicated. The stocksolutions obtained were diluted with an aqueous mixture containingacetone, water, isopropyl alcohol, dimethyl sulfoxide, Atplus 411F cropoil concentrate, and Triton X-155 surfactant in a48.5:39:10:1.5:1.0:0.02 v/v ratio to obtain spray solutions of knownconcentration. The solutions containing the highest concentration to betested were prepared by diluting 2 mL aliquots of the stock solutionwith 13 mL of the mixture and lower concentrations were prepared bydilution of appropriate smaller portions of the stock solution.Approximately 1.5 mL aliquots of each solution of known concentrationwere sprayed evenly onto various test plants using a Cornwall™ glasssyringe fitted with a TeeJet™ TN-3 hollow cone nozzle so as to obtainthorough coverage of each plant. Control plants were sprayed in the samemanner with the aqueous mixture. In this test an application rate of 1ppm results in the application of approximately 1 g/Ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 2 weeks the condition of the test plants comparedto that of the untreated plants was determined visually and scored on ascale of 0 to 100 percent, where 0 corresponds to no injury and 100corresponds to complete kill. Some of the compounds tested, applicationrates employed, plant species tested, and results are given in Table II.

                                      TABLE II                                    __________________________________________________________________________    POSTEMERGENCE HERBICIDAL ACTIVITY                                                Dose          Lambs-                                                                            Morn-  Vel-    Wild    Giant                                                                             John-                         Cpd.                                                                             Rate,                                                                             Cockle-                                                                            Jimson-                                                                            quar-                                                                             ing-                                                                              Pig-                                                                             vet-                                                                              Vero-                                                                             buck-                                                                             Black                                                                             Fox-                                                                              son-                                                                              Wild                      No.                                                                              PPM bur  weed ters                                                                              glory                                                                             weed                                                                             leaf                                                                              nica                                                                              wheat                                                                             grass                                                                             tail                                                                              grass                                                                             oats                                                                             Corn                                                                              Wheat              __________________________________________________________________________     1  500                                                                              35   50   75  75  85 85  85  80  50  35   0  65  0  35                  3  125                                                                              90   80   85  100 100                                                                              80  --  80  80  30  80  70 85  35                    15 6                                                                              90   70   80  78  80 78  --  70  75  0   70  40 40  0                   4  125                                                                              100  95   85  85  100                                                                              65  95  95  70  50  70  60 85  30                  5  500                                                                              30   25   35  --  50 65  15  40   0  0    0   0 30  0                   7 1000                                                                              75   35   70  --  80 45  50  75  25  0    0   0  0  0                   9 1000                                                                              35   25   80  --  90 65  40  80  35  0    0   0  0  0                  11  125                                                                              90   90   80  100 90 80  80  75   0  50  50   0 80  10                 13  125                                                                              70   70   70  85  90 30  50  80   0  0   20   0  0  20                 15  125                                                                              95   80   80  80  90 70  --  80  85  30  90  80 90  0                  17  125                                                                              40   70   50  70  80 60  80   0   0  0    0   0 10  0                  19  125                                                                              80   85   80  90  80 80  --  80  80  0   78  65 35  0                  21 1000                                                                              100  90   80  90  100                                                                              98  100 95  80  70  50  30 85  0                  23  500                                                                              85   75   85  --  95 80  95  95   0  0    0   0 20  0                  25 2000                                                                              80   75   80  70  70 90  90  80  20  0    0  30  0  0                  27 1000                                                                              80   70   80  90  90 70  --  80  40  0   70   0 20  40                 29 1000                                                                              80   80   85  85  100                                                                              85  75  80   0  0    0   0  0  15                 31 2000                                                                              90   80   70  90  90 80  70  98  40  0    0   0 50  0                  33 1000                                                                              50   80   50  50  45 40  55  50   0  30   0   0 55  0                  35 1000                                                                              65   75   85  85  95 50  55  85   0  0    0   0 10  0                  37 1000                                                                               0   75   75  50  55 80  100 90   0  15   0   0  0  15                 39  500                                                                               0   35   75  15  75 45  50  75  25  0   10  10 10  30                 40  500                                                                               0   35   75  30  30 20  85  85  45  30  35  20 75  30                 41  125                                                                              100  80   80  65  100                                                                              70  100 100 25  0   55  40 75  0                  42  125                                                                              80   75   85  75  75 60  70  80  35  0   35  30 80  0                  43  500                                                                              85   90   90  100 85 85  100 85  85  80  95  65 95  55                 44  500                                                                               0   15   80  30  75 20  70  55  15  25  75  20 40  25                 45 2000                                                                              80   95   90  25  100                                                                              90  95  90  35  25  50  15 40  15                 46 1000                                                                              35   55   85  25  75 50  75  70  15  0   75  15 75  0                  49 1000                                                                              85   100  90  75  95 85  95  90  15  0    0  10 25  0                  51 1000                                                                              65   90   90  65  100                                                                              90  100 90  25  0    0  25 20  0                  52 2000                                                                               0    0   80   0  30 85  35  25  15  0    0   0  0  0                  54 1000                                                                              65   85   85  35  95 80  100 75  20  0   35   0 65  0                  55 1000                                                                              60   20    0  70  40 65  50  20   0  0    0   0  0  0                  57 2000                                                                              80   80   85  95  100                                                                              80  85  90   0  25   0   0  0  0                  58 1000                                                                              95   100  95  100 100                                                                              95  100 95  50  35  50  35 50  35                 59  500                                                                              85   85   95   0  95 75  85  80  20  25  30  45 85  5                  60 2000                                                                               0    0   85  85  50 80  50  35   0  10   0   0 40  20                 61 2000                                                                               0    0   80  80  90 70  80  85  20  50   0  85 50  20                 62 2000                                                                              50   20   80  80  80 80  30  50  10  0    0  30  0  0                  63 2000                                                                               0    0   85  90  30 30  20  50   0  25  10   0 20  10                 65 2000                                                                               0   40   70  90  20 20  20   0   0  0    0   0  0  0                  67 1000                                                                              40   30   80  60  55 75  70  --  80  78  80  80 30  65                 __________________________________________________________________________

Example 8 Preemergence of Herbicidal Activity

Seeds of the desired test plant species were planted in sandy soilhaving a pH range of about 5-7.5 and an organic matter content of lessthan 1.0 percent in plastic pots with a surface area of 103 square cm.The pots were maintained in a greenhouse with an approximately 14 hrphotoperiod maintained at about 25°-33° C. during the day and 15°-20° C.during the night. Nutrients were added on a regular basis andsupplemental lighting was provided with an overhead 1000 Wattmulti-vapor lamp when necessary.

A weighed amount of each test compound in a 10 mL glass vial wasdissolved in 8 mL of a 97:3 mixture of acetone and dimethyl sulfoxide toobtain concentrated stock solutions. If the test compound did notdissolve readily, the mixture was warmed and sonicated. The stocksolutions obtained were diluted with a 99.0:0.1 mixture of water andTween™ 20 to obtain application solutions of known concentration. Thesolutions containing the highest concentration to be tested wereprepared by diluting 4 mL aliquots of the stock solution with 8.5 mL ofthe mixture and lower concentrations were prepared by dilution ofappropriate smaller portions of the stock solution. A 2.5 mL aliquot ofeach solution of known concentration was sprayed evenly onto the soil ofseeded pots using a Cornwall™ glass syringe fitted with a TeeJet™ TN-3hollow cone nozzle so as to obtain thorough coverage with a known amountof each test compound. Control plants were sprayed in the same mannerwith the aqueous mixture.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by top-irrigation. After 3 weeks thecondition of the test plants compared to that of the untreated plantswas determined visually and scored on a scale of 0 to 100 percent, where0 corresponds to no injury and 100 corresponds to complete kill. Some ofthe compounds tested, application rates employed, plant species tested,and results are given in Table III.

                                      TABLE III                                   __________________________________________________________________________    PREEMERGENCE HERBICIDAL ACTIVITY                                              Cpd.                                                                             Dose Rate,                                                                          Morning-                                                                           Pig-                                                                              Velvet-                                                                            Wild Buck-                                                                          Black                                                                             Barnyard                                                                           Giant                                                                             Johnson-                            No.                                                                              Kg/Ha glory                                                                              weed                                                                              leaf wheat grass                                                                             Grass                                                                              Foxtail                                                                           grass                                                                              Corn                                                                             Wheat                       __________________________________________________________________________     3 2.24  85   90  90   85    85  70   60  --   95 75                          15 2.24  85   100 30   100   95  80   80  95   95 100                         17 2.24   0   60   0    0     0   0    0   0    0  0                          19 2.24  95   95  85   80    75  70   50  95   75 75                          21 2.24  85   100 70   100   55  75   15  65   90  0                          23 4.48  50   90  30   90    50  40   20  30   20  0                          27 4.48  115  100  0   75    45  75   50  65   25 10                          31 4.48  65   95   0   45     0  15    0  --    0  0                          39 4.48  20   30  20   70    40  20   40   0   20  0                          40 4.48  80   95  40   --    60  90   70  75   95 70                          41 1.12  90   98  95   --    80  50   50  75   90 70                          42 2.24  90   98  85   --    90  70   75  80   95 70                          43 2.24  85   95  90   --    85  85   85  85   95 70                          44 4.48  60   98  30   --    80  75   40  85   90 75                          45 4.48  70   90  50   50    80  20   40  50   70 30                          46 4.48  30   50   0   70    70  30    0  70   20 10                          49 4.48  90   100 70   --    20   0   20   0   40 10                          51 4.48  75   95  95   50    70  40   30  90   40 20                          54 4.48  20   90  20   80     0   0    0  40    0 10                          59 4.48  --   95  60   --    60  40   30  60   60 30                          __________________________________________________________________________

What is claimed is:
 1. A compound of the formula ##STR5## wherein Q andQ' both represent N;Y and Y' each independently represent H, R¹, OR¹,SR¹, NR² ₂, F, Cl, or Br; X¹ and X⁵ each independently represent H, F,Cl, Br, or (C₁ -C₄)alkyl optionally mono- or disubstituted withfluorine; X² and X⁴ each independently represent H, F, Cl, Br, (C₁-C₄)alkyl optionally mono- or disubstituted with fluorine, SR¹, OR¹, orO-phenyl, O-pyridinyl, or O-pyrimidinyl each optionally substituted withup to two substituents selected from F, Cl, Br, CF₃, CH₃, and CN; X³represents H or F; with the proviso that of X¹, X², X³, X⁴, and X⁵ atleast two represent H and at least three represent H or F; Z representsO or S; R represents H, (C₁ -C₃)alkyl, CO₂ H, CN, CF₃, or F; R¹represents (C₁ -C₃)alkyl optionally singly to completely substitutedwith fluorine; and R² represents H or (C₁ -C₃)alkyl;or an agriculturallyacceptable salt, ester, or amide thereof.
 2. A compound according toclaim 1 wherein Z represents
 0. 3. A compound according to claim 1wherein X¹ represents F and X², X³, X⁴, and X⁵ represent H; wherein X²represents F and X¹, X³, X⁴, and X⁵ represent H; or wherein X¹ and oneof X⁴ and X⁵ represent F and X², X³ and the other of X⁴ and X⁵ representH.
 4. A compound according to claim 1 wherein Y and Y' eachindependently represent H, CH₃, or OCH₃.
 5. A compound according toclaim 1 wherein R represents H.
 6. A compound according to claim 1 inthe form of an agriculturally acceptable salt, ester, or amide.
 7. Acompound according to claim 6 wherein the compound is in the form of a(C₁ -C₈)alkyl or (C₃ -C₈)alkoxyalkyl ester.
 8. A compound according toclaim 6 which is an agriculturally acceptable ester of2-(2-fluorophenoxy)-2-(4,6-dimethyl-1,3,5-triazin-2-yloxy)acetic acid.9. An herbicidal composition comprising an agriculturally acceptableadjuvant or carrier in admixture with an herbicidal amount of a compoundof the formula ##STR6## wherein Q and Q' both represent N;Y and Y' eachindependently represent H, R¹, OR¹, SR¹, NR² ₂, F, Cl, or Br; X¹ and X⁵each independently represent H, F, Cl, Br, or (C₁ -C₄)alkyl optionallymono- or disubstituted with fluorine; X² and X⁴ each independentlyrepresent H, F, Cl, Br, (C₁ -C₄)alkyl optionally mono- or disubstitutedwith fluorine, SR¹, OR¹, or O-phenyl, O-pyridinyl, or O-pyrimidinyl eachoptionally substituted with up to two substituents selected from F, Cl,Br, CF₃, CH₃, and CN; X³ represents H or F; with the proviso that of X¹,X², X³, X⁴, and X⁵ at least two represent H and at least three representH or F; Z represents O or S; R represents H, (C₁ -C₃)alkyl, CO₂ H, CN,CF₃, or F; R¹ represents (C₁ -C₃)alkyl optionally singly to completelysubstituted with fluorine; and R² represents H or (C₁ -C₃)alkyl;or anagriculturally acceptable salt, ester, or amide thereof.
 10. Acomposition according to claim 9 wherein Z represents O.
 11. Acomposition according to claim 9 in the form of an agriculturallyacceptable salt, ester, or amide.
 12. A composition according to claim11 wherein Z represents O; both Q and Q' represent N; X¹ represents Fand X², X³, X⁴, and X⁵ represent H or X² represents F and X¹, X³, X⁴,and X⁵ represent H, or X¹ and one of X⁴ and X⁵ represent F and X², X³and the other of X⁴ and X⁵ represent H; Y and Y' each independentlyrepresent H, CH₃, or OCH₃ ; and R represents H.
 13. A method ofcontrolling undesirable vegetation which comprises contacting thevegetation or the locus thereof with an herbicidal amount of a compoundof the formula ##STR7## wherein Q and Q' both represent N;Y and Y' eachindependently represent H, R¹, OR¹, SR¹, NR² ₂, F, Cl, or Br; X¹ and X⁵each independently represent H, F, Cl, Br, or (C₁ -C₄)alkyl optionallymono- or disubstituted with fluorine; X² and X⁴ each independentlyrepresent H, F, Cl, Br, (C₁ -C₄)alkyl optionally mono- or disubstitutedwith fluorine, SR¹, OR¹, or O-phenyl, O-pyridinyl, or O-pyrimidinyl eachoptionally substituted with up to two substituents selected from F, Cl,Br, CF₃, CH₃, and CN; X³ represents H or F; with the proviso that of X¹,X², X³, X⁴, and X⁵ at least two represent H and at least three representH or F; Z represents O or S; R represents H, (C₁ -C₃)alkyl, CO₂ H, CN,CF₃, or F; R¹ represents (C₁ -C₃)alkyl optionally singly to completelysubstituted with fluorine; and R² represents H or (C₁ -C₃)alkyl;or anagriculturally acceptable salt, ester, or amide thereof.
 14. A methodaccording to claim 13 wherein Z represents O.
 15. A method according toclaim 13 wherein the compound is in the form of an agriculturallyacceptable salt, ester, or amide.
 16. A method according to claim 15wherein Z represents O; both Q and Q' represent N; X¹ represents F andX², X³, X⁴, and X⁵ represent H or X² represents F and X¹, X³, X⁴, and X⁵represent H, or X¹ and one of X⁴ and X⁵ represent F and X², X³ and theother of X⁴ and X⁵ represent H; Y and Y' each independently represent H,CH₃, or OCH₃ ; and R represents H.